Azo dye of the pyrazolone type



Patented Feb. 29, 1944 NITED 2,343,234 AZO DYE OF THE PYRAZOLONE TYPE James ll. Williams, Riverside, Conn., assignor to American Cyanamid 00., New York, N. Y., a corporation of Maine No Drawing. Application August 20, 1941, Serial No. 407,649

3 Claims. (Cl. 260162) This invention relates to azo dyes derivable from sulfanilyl pyrazolones.

A new series of azo dyes can be prepared utilizing sulfanilyl pyrazolones as one of the dye Example 3 A diazo solution was Example 1 and was then coupled With gamma 32 zgz ggi gi i ggz fig gi w to 5 gamma acid dissolved in 270 parts of water b containing 15 parts of soda ash Acetic acid $132 was then added untll the solution was acid to a in which R is an aryl radical which may or may methyl -y l ow ndi a r pap r. Ice was not contain further azo groups d Spz is t m then added to cool to C. and the diazo soluradical of sulfanilyl pyrazolona tion introduced into the slurry. Coupling In general two sub-classes of dyes can be started and there was a dark red precipitate, made because sulfanilyl pyrazolones can either COUDII'IIg b81115 p e ed by a l win to Stand be diazotized and coupled with the usual couovernight at 10 C. The product Was a Waterpling components or aromatic amines can be Soluble, brick red y diazotized and. coupled to the sulfanilyl py- Example 4 razolones. Polyazo dyes can of course, be made by diazotizing aromatic amines coupling to the parts of sulfamlamlde were dlssolved 1n pyrazolones and then diazotizing the primary 200 Of Water with cc. concentrated C. P. amino group on the sulfanilyl radical and couan 011 f ng to 5 C., diazotization was pling that with .further coupling components. earned out the manner Wlth 109 Parts The dyes are, for the most part, of various of normal n1t1'1te $1l1t10nshades of red and yellow depending on the cou- Meanwhlle solution In NaOH 0f the pyrazpling components, or diazotized amines. In 010F161 was made as follows! parts of Sulfgeneral the fi t group r f d to above anilyl pyrazolone was dissolved in 200 cc. of duces more reddish shades and the second group 25 Water by heatmg Wlth 20 parts 5 NaOH- Then more yellowish shades. The invention will be parts 10% SOda ashWaS addei After 0001- described in greater detail in conjunction with to the above dlaZO was added and 0011- the following pecifi examples pling ensued almost at once. The product was slightly soluble in the alkaline coupling medium Example 1 30 but on acidification it was entirely precipitated 76 parts of 1-sulfani1y1-3-methyl-5-pyrazoas a pale yellow product. lone were dissolved in 600 parts of water with 45 This product was soluble in alcohol and ether parts of HCl. The solution was then cooled to as a beautiful bright greenish yellow. 5 C. with ice and diazotized with 20.7 parts of I claim: sodium nitrite at 5-8 C. After diazotization 1. An azo dye having the following formula: the mixture was run slowly into a solution to 45 N=C CH: parts of beta-naphthol in 132 parts of 10% sodium hydroxide solution to which 50 parts of a I 10% soda ash solution had been added. The c cH, reaction mixture was cooled to 0 C. by means of OH 3 ice. Coupling took place almost instantly and the product was insoluble and was recovered by filtration. It was orange in color and soluble in alcohol and ether The compound t 2. An azo dye having the followmg formula: probably had the following formula:

C CH3 R-N=NS OzPz N=NSO2N\ in which R is a radical of an azo coupling comc-cm ponent of the naphthalene series and P2 is a 0B g pyrazolone radical.

3. An azo dye having the following formula:

N=CCH: Example 2 RN=NSOzN I A diazo solution was prepared as described in Example 1 and was coupled at 0 C. with a solu- H tion containing parts of an M Shaefiers salt, 5 parts of soda ash and parts of water; in which R is a radical of an azo coupling comcoupling was rapid and the product obtained 60 ponent of the naphthalene series.

was partially water soluble and dyed wool bright yellowish o orangish shades.

JAMES H. WILLIAMS. 

